Work Text:
You were Handsome Jack’s new personal assistant. And as his personal assistant, after your predecessor’s unfortunate ‘accident’ involving an airlock, your job was to keep Handsome Jack happy. Unsurprisingly, this was a more difficult task than it sounded, and sometimes it involved some… less than HR-friendly activities. But you didn’t necessarily have a problem with those. You did have a problem with his volatile temperament, but nonetheless - you tolerated all of his outbursts, agreed with everything he said no matter how ridiculous, or vain, or needlessly cruel, and sometimes even got along with him, briefly.
It wasn’t easy work, but it was work.
And on this particular day, work meant testing a new piece of Hyperion technology at Jack’s request. On him. That would be incredibly strange, if this particular device wasn’t a vibrator.
It was one-of-a-kind, commissioned specifically for him, and it was more powerful than anything of its size currently out on the market. So powerful, in fact, that you could barely feel your hands as you held it, straddling his thighs in his locked office and watching him ride out the aftershocks of his orgasm with a little more interest than usual.
But before you could shut it off and move on, an idea occurred to you. What if you just… didn’t? He’d seemed open to the concept when the two of you discussed limits (a given, upon accepting the job), and this could make it a lot more fun. Or you’d get fired and possibly die, but as it stood, you liked your odds.
So you took the risk.
“Oh boy, kitten, that’s… that’s a lot. You can turn it off now.” You could hear the effort it took for him to keep his voice steady, even as he twitched and jerked away from the device in your hand, and when you didn’t let up, he actually started to look a bit worried, “C’mon, I don’t know what you’re trying to prove here, but you’ve made your point.”
You smiled politely at him then, finger hovering over the controls, and waited for him to realize what you had in mind. It didn’t take long.
His eyes widened for a split second, momentary panic before he schooled his expression again and you saw something else underneath - something that made you think this could really be worth it.
So when he managed to ask you: “You really wanna do that?”
You decided that you did. Giving the button a few clicks kicked the speed up significantly, and from there he lost his ability to form any coherent speech at all.
He writhed, head thrown back in an overwhelming mix of pleasure and pain. One hand flew up to cover his mouth in an attempt to stifle the undignified noises he couldn’t seem to stop making, while the other was busy trying (and failing) to somehow get the vibrator away from his dick. At the very least, if he decided to kill you for this, you’d die knowing what a raging megalomaniac looked like in the throes of overstimulation, and that was consolation enough.
But the strange thing was, you figured if he was going to kill you, you’d know by now. There was nothing stopping him from pushing you off, murdering you for emasculating him, and then launching you out into the cold expanse of space, but he wasn’t doing any of that.
Instead, what you got was a pleading, whimpering mess, now nearly on the verge of tears because it all felt too intense and neither his mind nor his body knew how to cope. And the best part? The thing wasn’t even on the highest setting yet.
“Tell me what you want, you’ve gotta use your words sweetheart.” You purred, feeling him tremble underneath you. “S’ too much. Please. I can’t.” He panted, voice cracking. Knowing just as well as you did that unless the next thing that came out of his mouth was his safeword, Tassiter, anything he chose to say had no bearing. “Aw, but I think you can handle a bit more, can’t you? You’re doing so well.”
Jack let out a pained whine, still half-heartedly trying to squirm away from it. You knew it was all for show, but your own peace of mind required you to check in anyways.
“You know what to say if you need this to stop, right?”
He nodded, but that wasn’t good enough. “What’d I say? I need a yes or a no.”
“Sure, yeah, I know it! Don’t kill the mood.” Jack huffed, and you had to admit, watching him try to act annoyed when he looked like he could barely remember his own name was the most arousing thing you’d seen in a very long time. Wanting to take advantage of the moment, you upped the speed again, and anything else he might have said devolved into a litany of curses. “I don’t think you can accuse me of ‘killing the mood’ when I’m about to make you cum. And watch your language, pumpkin.”
That elicited a sharp gasp from the man, his hips bucking of their own accord, and as hard as he bit down on his tongue, muting himself proved to be impossible. Not like that was out of character for him, but of course when you actually wanted him to be loud, he had to make it difficult and develop a sense of shame for the first time in his life. “Come on… you moan so pretty, I wanna hear it.”
“Ffffughhh, I’m just- I’m close. Again.” He whimpered, refusing to meet your eyes. Seeing him in this moment, you realized that he almost didn’t even look like himself when he wasn’t posturing. He was smaller, softer in a way you’d never seen him before now. Truth be told, you liked him better like this. “Go ahead, whenever you’re ready. You’ve been so good for me today, Jack.”
He cried out, his second climax hitting him like a brick wall, and it sounded half like a sob. His head fell to your shoulder. You could feel the warmth of his breath through the fabric, fast and hard at first, and evening out once you hit the power button and he started to come back down.
The two of you stayed like that for longer than you’d have expected, though it still wasn’t very long. After a minute or two, you pulled away, and that other Jack was gone in an instant.
He sat up straight, righting himself as best as he saw fit while you did the same, though you knew that the very next thing he’d be asking for was a new shirt and pants given the state of those ones. He looked you up and down. At the very least, he looked pleased.
“Jeez, that was… wow. I guess I‘ll have to keep you around after all.”
With that glowing review, you were dismissed for more important work, like finding new clothes that didn’t have cum on them, and getting him a coffee. But it stuck with you, long after you got home that night.
Maybe there was a human being somewhere under the mask. And maybe if you broke Handsome Jack down enough, you’d find him.